I subscribe to the camp that believes that flats should never be basic. Unlike heels, flats have to draw visual interest from something other than an alluring curve or straight up sex appeal. Basic black might be practical, but it's boring as hell. The same black flats would be just as practical in quilted patent leather, or with a buckle, bow, or reverse stitching.
So, we come to rule number 1: Even when practicality is your first priority, shape, pattern, and texture should be considered, too.
Some basic black flats that hit the mark:
Why do these work, you ask? The first is a Steve Madden in tweed with a buckle accent. These would work with skirts, dresses, jeans, whatever. A round toe is super practical and the shoe is cute without looking like something you stole from your kid sister.
The second is a pointy toed Report, with a grommeted buckle and a subtle shape that gives it just a hint of sex appeal. This shoe is also practical without putting anyone with eyes to sleep.
The third is the Tory Burch Reva ballerina flat. This one comes in suede and has the signature medallion on the toe. There are countless knockoffs of this shoe, so don't let the $195 price tag of this one scare you. Looks comfy and practical to me, but it screams fashion conscious without being obnoxious.
Rule number 2: Color and pattern can make a basic outfit interesting- embrace them on your tootsies.
Check these out:
I recommend jumping on Zappos.com immediately to check out this first pair- they are from Fitzwell Callie, come in like ten colors, and are $65.
If you are a prepster like my li'l sis, you will recognize a boat shoe with you see one. The second pair above are in rust, the brand is Unisa, and they are perfect for pants and skirts this fall.
Animal print is awesome, especially in a sleek black and white pair like the third pair above. Guaranteed to make your outfit pop, these Sigerson Morrisons are amazing. Don't pay $500 for yours, though- I've seen pairs at every price point in stores and on Zappos.
The fourth pair is the DKNY Brianna in grape patent python. The d'orsay cut out gives the shoe some sex appeal, and the color is fun without being loud. Not only is this one way to wear purple if you aren't sure about the purple trend this season, it is a way to add color and texture in one purchase. These also come in black, orange, and yellow.
Rule number 3: Sporty and weekend flats should not look juvenile or orthopedic.
The first pair is from Privo, a quality brand of comfortable, sporty shoes that aren't bulky. These stay sleek and light: perfect for running errands or as your commute shoe.
The second pair is from Hush Puppies, so you know it's comfy. It is also polished and great with jeans.
The red and white pair tows the line between adult and just for kids. I like a printed shoe with a bow, just make sure the lines are simple and there isn't any other embellishment. From Unlisted.
The last pair is from Kenneth Cole Reaction and I love that it is neutral but not sleep-inducing, since it has a subtle pattern. It comes in 3 other equally neutral and subtle patterns and is only $73.
Other brands to consider: Simple, Grasshoppers, Keds, Naturalizer. The question to ask before buying: Do 16 or 60 year olds wear this? If yes, move on, people.
Rule number 4: if you are short, want your legs to look longer, or tend to wear longer skirts: Beware.
Nothing lengthens your silhouette and legs like heels. So if you wear flats, try a pointy-toed shoe and avoid an ankle strap like the plague.
If you wear skirts below the knee, you will look shorter and squatter with flats.
The general rule for skirt length vs. shoe height is the shorter the length, the flatter the shoe. Thus, the longer the length, the higher the shoe. This is a basic rule of proportion and balance the can't be denied unless you are over 5'10''. So keep your skirt length at or above the knee and you can avoid the dowdy school marm look that screams "celibate for life."